A highly efficient and stereoselective cycloaddition of nitrones to N-arylitaconimides |
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| Affiliation: | 1. Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai, 600 025, India;2. Chemical Technology Group R&D, SRF Limited, Jhiwana, Tijara, Bhiwadi, Rajasthan, 301 019, India |
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| Abstract: | The 1,3-dipolar cycloaddition of keto- and aldonitrones with N-arylitaconimides proceeds regioselectively giving only 5-spiroisoxazolidines. In the case of aldonitrones the reaction proceeds with high diastereoselectivity. A range of the obtained adducts were subjected to reductive cleavage of the N O bond using zinc powder in acetic acid to give the corresponding spirolactones and 1,3-amino alcohols. |
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| Keywords: | Nitrones Itaconimides Cycloaddition Reduction |
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